A snow-covered building with illuminated windows and a ski lift in the foreground.

Search Vacation Homes in Winter Park

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Winter Park vacation homes

A wooden deck with two chairs and a white railing.

1. Hideaway Village Alpine 4 Split interior 2 bedroom, comfortable family rental

Hideaway Village Alpine 4 Split interior 2 bedroom, comfortable family rental
Hideaway Village
9.2 out of 10, Wonderful, (11 reviews)
"This was a great place for me and my family to stay. The place was clean, and great communication with the host."
United States
Danielle T.
The price is ￥16,958
￥42,960 total
includes taxes & fees
Oct 24 - Oct 25
Hideaway Village Alpine 4 Split interior 2 bedroom, comfortable family rental
A snow-covered residential area with multiple two-story buildings, a clear sky, and snow-capped mountains in the background.

2. Timbers 5-2 Luxurious 2 bedroom, private deck, forest view

Timbers 5-2 Luxurious 2 bedroom, private deck, forest view
Fraser
10.0 out of 10, Exceptional, (3 reviews)
"Good location, nice place. "
United States
ann b.
The price is ￥15,251
￥48,663 total
includes taxes & fees
Oct 24 - Oct 25
Timbers 5-2 Luxurious 2 bedroom, private deck, forest view
A stone wall with the inscription 'the Timberline' and a small lamp.

3. Timbers 9-4 New, spacious condo in Fraser, private deck and more!

Timbers 9-4 New, spacious condo in Fraser, private deck and more!
Fraser
8.0 out of 10, Very good, (1 review)
"The unit was clean and well appointed"
United States
Michael J.
The price is ￥16,441
￥51,056 total
includes taxes & fees
Oct 30 - Oct 31
Timbers 9-4 New, spacious condo in Fraser, private deck and more!
A cozy living room with a stone fireplace, wooden walls, a green sofa, and a view of a forest through large windows.

4. Hideaway Village Lenado 4 Lovely townhome, river views, 2 private decks

Hideaway Village Lenado 4 Lovely townhome, river views, 2 private decks
Hideaway Village
8.0 out of 10, Very good, (3 reviews)
"This location is fantastic. The house is dated and floors creak, but it fit our needs."
United States
Cambammo C.
The price is ￥15,096
￥40,306 total
includes taxes & fees
Oct 25 - Oct 26
Hideaway Village Lenado 4 Lovely townhome, river views, 2 private decks
A modern living room with a fireplace, a ceiling fan, and a view of the outside.

5. Downtown Winter Park Townhome, Rooftop Hot Tub, Dogs Welcome

Downtown Winter Park Townhome, Rooftop Hot Tub, Dogs Welcome
Winter Park
The price is ￥31,399
￥87,142 total
includes taxes & fees
Nov 10 - Nov 11
Downtown Winter Park Townhome, Rooftop Hot Tub, Dogs Welcome
A wooden deck with a single chair and table, overlooking a forested area.

6. RidgeView Retreat | Steps to Hideaway Park & Town

RidgeView Retreat | Steps to Hideaway Park & Town
Winter Park
10.0 out of 10, Exceptional, (2 reviews)
"A perfectly located townhome! A beautiful view from every window and a walk away from various food and trails/creeks. Would love to go back!"
United States
Martyna S.
RidgeView Retreat | Steps to Hideaway Park & Town
A wooden deck with a table and chairs, overlooking a scenic landscape with mountains and trees.

7. Epic Sunset Deck, Panoramic Mountain View’s. Ski, Hike, Bike, & Fish Winter Park

Epic Sunset Deck, Panoramic Mountain View’s. Ski, Hike, Bike, & Fish Winter Park
Fraser
10.0 out of 10, Exceptional, (12 reviews)
"Great location! Comfortable beds! Responsive host! Would definitely stay again! "
United States
Pamela D.
The price is ￥21,785
￥78,252 total
includes taxes & fees
Oct 24 - Oct 25
Epic Sunset Deck, Panoramic Mountain View’s. Ski, Hike, Bike, & Fish Winter Park
A wooden deck with a railing, a covered seating area, and a view of neighboring houses.

8. Close to slopes-Walk to Downtown Winter Park!

Close to slopes-Walk to Downtown Winter Park!
Winter Park
9.0 out of 10, Wonderful, (12 reviews)
"great location"
United States
Thomas B.
Close to slopes-Walk to Downtown Winter Park!
A modern two-story house with a dark exterior, a front door with a curtain, two potted plants, and a driveway leading to a garage.

9. 404 Doc Susie home Delightful and renovated home, walk to downtown, mt views

404 Doc Susie home Delightful and renovated home, walk to downtown, mt views
Downtown
The price is ￥24,434
￥69,342 total
includes taxes & fees
Oct 24 - Oct 25
404 Doc Susie home Delightful and renovated home, walk to downtown, mt views
A log cabin interior with a stone fireplace, a blue sofa, and a red armchair.

10. The Grand Timberglass Lodge | Tipi | Hot Tub

The Grand Timberglass Lodge | Tipi | Hot Tub
Winter Park
10.0 out of 10, Exceptional, (2 reviews)
"We had such a wonderful stay! We really liked this place. The highlight was definitely the breathtaking views - especially from the hot tub overlooking the mountains. Sauna was fantastic!! We will definitely be returning!! Thank you for sharing your home!!"
United States
Alan W.
The price is ￥24,544
￥81,133 total
includes taxes & fees
Oct 25 - Oct 26
The Grand Timberglass Lodge | Tipi | Hot Tub
A modern living room with a fireplace, a sofa, a coffee table, and a dining area with chairs and a table.

11. Private Hot Tub, Garage + EV Charger, On Bus Line!

Private Hot Tub, Garage + EV Charger, On Bus Line!
Fraser
10.0 out of 10, Exceptional, (3 reviews)
"The hot tub was great after a day of snowboarding!"
United States
Kale S.
The price is ￥19,836
￥57,180 total
includes taxes & fees
Oct 24 - Oct 25
Private Hot Tub, Garage + EV Charger, On Bus Line!
Where mountain views meet cozy evening ambiance.

12. Fresh Tracks @ Peak View Ridge

Fresh Tracks @ Peak View Ridge
Winter Park
10.0 out of 10, Exceptional, (5 reviews)
"Fresh Tracks @ Peak View Ridge will not disappoint! A brand new property, in pristine condition, with everything you could need! Host was very communicative and offered to assist if we were to need it, and the cleaning staff did a wonderful job preparing for us! Close to everything but not right on the main busy street in town. We absolutely loved the location and view! Can’t wait to stay here again!"
United States
Corrie W.
The price is ￥28,945
￥86,669 total
includes taxes & fees
Nov 10 - Nov 11
Fresh Tracks @ Peak View Ridge
A kitchen with wooden cabinets, stainless steel appliances, a granite countertop, and a window with a view of trees.

13. Meadow Ridge Court 29 unit 8 Lovely and spacious 3 bedroom family condo rental

Meadow Ridge Court 29 unit 8 Lovely and spacious 3 bedroom family condo rental
Fraser
6.0 out of 10, (1 review)
"At 1st glance the place looked pretty good. After getting settled in we found the place could use some tlc. Nothing major that ruined the stay but I was expecting more. Overall I would still recommend after it gets the attention it needs.The people I was in contact with were very friendly and helpful. "
United States
Rodney W.
The price is ￥25,523
￥61,350 total
includes taxes & fees
Oct 24 - Oct 25
Meadow Ridge Court 29 unit 8 Lovely and spacious 3 bedroom family condo rental
A balcony with two chairs, a view of a building with a red roof, and a clear sky.

14. Mountain escape, minutes from Winter Park resort and town. Hot tub access.

Mountain escape, minutes from Winter Park resort and town. Hot tub access.
Winter Park
9.6 out of 10, Exceptional, (7 reviews)
"Excellent stay!!"
United States
Ted W.
Mountain escape, minutes from Winter Park resort and town. Hot tub access.
A modern kitchen with a central island, a dining area with a sofa, and a large sliding glass door leading to a balcony.

15. Hot tub, 3 bedroom, Ski friendly, New build, 5 star Luxury Retreat

Hot tub, 3 bedroom, Ski friendly, New build, 5 star Luxury Retreat
Winter Park
10.0 out of 10, Exceptional, (1 review)
"Very well kept and well equipped. Excellent communication with owners. Very responsive to questions. Location is close to ski shuttle. 3 car covered garage. Hot tub A++++ Will stay again."
United States
Candice
Hot tub, 3 bedroom, Ski friendly, New build, 5 star Luxury Retreat
A wooden deck with a picnic table, a small table with a hat, and a chair.

16. 534 Sun River #8 Wonderful Fraser 2 bedroom, pet friendly, large yard

534 Sun River #8 Wonderful Fraser 2 bedroom, pet friendly, large yard
Downtown
8.6 out of 10, Excellent, (8 reviews)
"The property was amazing the view from the deck of the mountains had a spectacular sunset view. The home is very comfortable and welcoming we had a great evening making dinner and playing board games, the night we didn't cook there were plenty of great places a walk or short drive away, we highly recommend this place for your next stay and adventure at winter park."
United States
Steve P.
The price is ￥31,294
￥67,469 total
includes taxes & fees
Oct 24 - Oct 25
534 Sun River #8 Wonderful Fraser 2 bedroom, pet friendly, large yard
A wooden deck with a wicker chair, stone wall, and a view of neighboring houses.

17. Red Quill 707 Luxury downtown, private HT, garage parking, walk to main st

Red Quill 707 Luxury downtown, private HT, garage parking, walk to main st
Winter Park
The price is ￥38,399
￥87,120 total
includes taxes & fees
Oct 30 - Oct 31
Red Quill 707 Luxury downtown, private HT, garage parking, walk to main st
A living room with a fireplace, a sofa, a coffee table, and a view of mountains through a glass door.

18. The AlpenGlow House: Private Hot Tub Retreat with Stunning Mountain Views!

The AlpenGlow House: Private Hot Tub Retreat with Stunning Mountain Views!
Rendezvous
10.0 out of 10, Exceptional, (18 reviews)
"Amazing stay!!! Everything was as advertised!!Highly recommend!!"
United States
RW L.
The price is ￥24,685
￥79,213 total
includes taxes & fees
Oct 25 - Oct 26
The AlpenGlow House: Private Hot Tub Retreat with Stunning Mountain Views!
A modern kitchen with a built-in oven, a microwave, and a stove. There is a large window providing a view of the outdoors.

19. 881 Ermine Lane Outdoor hot tub, forest views, new construction vaulted ceilings

881 Ermine Lane Outdoor hot tub, forest views, new construction vaulted ceilings
Fraser
The price is ￥29,089
￥52,393 total
includes taxes & fees
Nov 6 - Nov 7
881 Ermine Lane Outdoor hot tub, forest views, new construction vaulted ceilings
A spacious living room with a stone fireplace, a dining area with a wooden table and chairs, and a large window offering a view of the outdoors.

20. Family-Friendly 3BR Mountain Condo – Pool, Hot Tub, Gym Near Winter Park

Family-Friendly 3BR Mountain Condo – Pool, Hot Tub, Gym Near Winter Park
Downtown
10.0 out of 10, Exceptional, (2 reviews)
"Perfect place to stay with young kids. Very baby friendly with all the essentials. Great communication with hosts. Has everything you need for your stay. Highly recommend! "
United States
Ashley L.
Family-Friendly 3BR Mountain Condo – Pool, Hot Tub, Gym Near Winter Park
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winter Park Hotel Reviews

Fraser Crossing Founders Pointe

Fraser Crossing Founders Pointe

10/10 Excellent
"Nice place in the mountains to stay"
emmanuel 3-night trip
Posted 16 hours ago
Fraser Crossing Founders Pointe

Find out more about Winter Park

Winter Park Vacation Homes information

Number of reviews
76
Accommodation
735 Vacation Homes
Lowest Price
￥40,306
Highest Price
￥87,120